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To pickpocket, Sly needs to get near the guard's pocket and press to swipe something out. While behind a guard, Sly will enter into his "Stealth Stance", where he is crouching. He will pickpocket with the crook of his cane. In Thieves in Time, Sly's ancestors can also pickpocket guards, using the same rules as Sly.

In Sly 3, Bentley can pickpocket once he has obtained the Pick Pocket Pole, which requires it to be assigned to a button (, , or ) via the Gadget Grid. When he is close enough to the guard, hold the assigned button, and then move back (or stay still if the guard is moving forward). The coins will come automatically. Bentley can also shoot a sleep dart at an enemy and then pickpocket them.

In Thieves in Time, Bentley uses the robotic arms in his wheelchair to pickpocket guards instead of the Pick-Pocket-Pole. Here, Bentley's version of pickpocketing is exactly the same as Sly's version, right down to pressing to pickpocket.

Unlike Sly and Bentley, Murray's version of pickpocketing is more overt. It does not matter whether Murray has alerted guards or not to pickpocket, unless he wants to pickpocket a flashlight guard, in which he must not alert them. In Sly 3, while behind a guard, uppercut him with the , then grab him out of the air with the . While in Murray's grasp, press multiple times to shake the guard loose of his coins and loot. If a foe is on the ground and dazed, Murray can stomp to pick up his victim by pressing , before proceeding to press it again to pickpocket.

In Thieves in Time, Murray retains the ability to pickpocket, but with a few changes. Since Murray cannot perform uppercuts in this game, Murray's stomp () has been buffed to allow him to pick up foes in the same way he would an object. As with Sly 3, Murray has to press while carrying a guard to start shaking loose coins. However, you cannot steal loot from guards by default. In order to be able to steal loot, you will need to purchase the Looty Shake power-up from ThiefNet.

In Thieves in Time, Carmelita is the only character that cannot pickpocket.

In Sly 2, Bentley can sell the loot Sly obtains on ThiefNet for coins, while from Sly 3 forward, the items' value is automatically added to the player's coins.

In Sly 3, the coins that Murray shakes out of a guard drop to the ground, making it necessary to collect the coins after shaking them out. This can lead to situations where the dropped coins are unobtainable, such as shaking a guard while facing and standing near open water, or while right next to a wall.